Literature DB >> 17900130

Stereoselective synthesis of 2,3-unsaturated-aza-O-glycosides via new diastereoisomeric N-Cbz-imino glycal-derived allyl epoxides.

Valeria Di Bussolo1, Annalisa Fiasella, Maria Rosaria Romano, Lucilla Favero, Mauro Pineschi, Paolo Crotti.   

Abstract

Diastereoisomeric D,L-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined. The reactions lead to the corresponding 2,3-unsaturated-aza-O-glycosides through a new, completely regioselective 1,4-addition process which proceeds with complete substrate-dependent stereoselectivity.

Entities:  

Year:  2007        PMID： 17900130     DOI： 10.1021/ol701836a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors:  Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

2.  Synthesis and structure-activity relationship studies of novel dihydropyridones as androgen receptor modulators.

Authors:  Antonella Pepe; Michael Pamment; Yeong Sang Kim; Sunmin Lee; Min-Jung Lee; Kristin Beebe; Anton Filikov; Len Neckers; Jane B Trepel; Sanjay V Malhotra
Journal:  J Med Chem       Date:  2013-10-30       Impact factor: 7.446

3.  Enantioselective synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes.

Authors:  Adwait R Ranade; Gunda I Georg
Journal:  J Org Chem       Date:  2014-01-13       Impact factor: 4.354
  3 in total

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